H-beta,beta-Dicyclohexyl-DL-Ala-OH is a modified alanine derivative in which the β,β-dicyclohexyl substitution replaces the native side-chain environment, yielding a sterically encumbered, nonstandard α-amino acid framework. The molecule contains a free α-amino group and a free carboxylic acid (-COOH) on the alanine backbone, with the "DL" designation indicating a racemic mixture at the α-carbon while the bulky cyclohexyl groups at the β,β positions provide pronounced hydrophobic character and conformational restriction. As a structurally modified amino acid, it is used as a building block for peptide and peptidomimetic synthesis and for structure-activity or binding studies where β,β-disubstitution and increased steric bulk are used to probe effects on conformation, presentation of functional groups, and intermolecular interactions.
CAT No: CP26935
CAS No:274262-70-3
Synonyms/Alias:274262-70-3;H-DL-Ala(dicyclohexyl)-OH;SCHEMBL2679604;BETA,BETA-DICYCLOHEXYL-DL-ALANINE;OR251532;H-BETA,BETA-DICYCLOHEXYL-DL-ALA-OH;RT-013200
H-beta,beta-Dicyclohexyl-DL-Ala-OH is a DL-alanine derivative bearing a substituted β,β-dicyclohexyl motif that replaces the native side-chain environment with bulky, hydrophobic cyclohexyl groups while retaining the α-amino acid framework with a free carboxylic acid and an amino functionality. The stereochemistry is specified as DL, indicating a racemic mixture at the α-chiral center, which affects diastereoselective outcomes in peptide coupling and downstream separations. The compound's high steric bulk and increased lipophilicity influence amide formation rates, protecting-group stability, and conformational preferences of resulting peptide analogs. As an amino acid building block and chiral synthesis intermediate precursor, it can be directed into protected amino acid forms to support controlled peptide construction and functional group transformations.
1. Peptide Synthesis
H-beta,beta-Dicyclohexyl-DL-Ala-OH is used in peptide synthesis workflows where alanine-like α-amino acid reactivity is required alongside a strongly hydrophobic β,β-dicyclohexyl side-chain. The free carboxylic acid and amino functionality can be converted into peptide-compatible derivatives, such as N-protected amino acids and activated C-termini, enabling standard peptide coupling chemistries to form amide bonds at the α-position. The racemic (DL) stereochemical character supports generation of mixed stereoisomer peptide libraries for conformational and hydrophobicity mapping. Downstream, incorporated residues can be used to tune folding propensity, increase membrane affinity of peptide analogs, and provide scaffold diversity for structure-activity relationship studies in peptide science.
2. Peptidomimetics
H-beta,beta-Dicyclohexyl-DL-Ala-OH serves as a feedstock for peptidomimetic construction in which side-chain sterics and hydrophobic surface area are engineered to emulate non-natural residue behavior. The β,β-dicyclohexyl substitution creates a bulky, conformationally biasing substituent that can be carried into amide-linked analogs, helping define local geometry and resistance to proteolytic recognition. The amino acid backbone allows incorporation into protected building-block sequences, while the carboxylic acid enables subsequent derivatization to amides, esters, or linkers used in scaffold diversification. Resulting peptidomimetics can be advanced as chemical biology probes and SAR-focused intermediates where side-chain topology is the primary design variable.
3. Chiral Building Block Development
H-beta,beta-Dicyclohexyl-DL-Ala-OH is applicable to chiral synthesis and resolution strategies because the α-stereocenter is present as a DL mixture that can be separated or transformed into enantiopure derivatives. The amino acid functionality supports conversion to chiral auxiliary or temporary stereocontrol elements through N-protection and carboxyl activation, enabling downstream asymmetric coupling or separation workflows. The persistent β,β-dicyclohexyl group provides a sterically demanding handle that can influence crystallization behavior and diastereomeric salt formation during resolution. Enantiopure derivatives generated from this racemate can then be used as stereochemically defined amino acid building blocks for enantioselective peptide coupling and mechanistic studies in stereochemical amino acid chemistry.
4. Side-Chain Functionalization
H-beta,beta-Dicyclohexyl-DL-Ala-OH can be employed for amino acid derivatization routes that introduce additional functionality onto the carboxyl group or through controlled transformations of the protected amino acid intermediate. The α-carboxylic acid can be converted into activated esters or amide-forming derivatives to generate conjugation-ready intermediates, while N-protection strategies allow selective chemistry without interfering with peptide coupling sites. The β,β-dicyclohexyl motif provides a hydrophobic anchor that can be leveraged to tune solubility, partitioning, and binding-site hydrophobic contacts in synthetic constructs. Downstream products include linker-bearing amino acid analogs, hydrophobic tags for biomolecule labeling workflows, and intermediate materials for fine chemical synthesis where side-chain sterics govern reactivity and molecular recognition.
5. Process Chemistry Intermediate
H-beta,beta-Dicyclohexyl-DL-Ala-OH is suitable for process chemistry intermediate preparation where robust amino acid handling and predictable functional group interconversions are required at scale. The compound's amino acid structure supports standard industrial protection/activation logic, including conversion to N-protected forms and carboxyl activation for controlled downstream coupling steps. The bulky β,β-dicyclohexyl substituent can be advantageous for reproducible physical properties of protected intermediates, aiding isolation and purification in multi-step manufacturing sequences for peptide building blocks. Resulting protected amino acid derivatives can serve as manufacturing inputs for peptide analog production, peptidomimetic synthesis, and other specialty chemical production streams that rely on consistent amino acid chemistry and scalable intermediate transformations.
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